WO2021244951A1 - Fungicidal compositions - Google Patents
Fungicidal compositions Download PDFInfo
- Publication number
- WO2021244951A1 WO2021244951A1 PCT/EP2021/064261 EP2021064261W WO2021244951A1 WO 2021244951 A1 WO2021244951 A1 WO 2021244951A1 EP 2021064261 W EP2021064261 W EP 2021064261W WO 2021244951 A1 WO2021244951 A1 WO 2021244951A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- difluoro
- pyridyl
- compound
- amino
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Definitions
- the present invention relates to novel fungicidal compositions, to their use in agriculture or horticulture for controlling diseases caused by phytopathogens, especially phytopathogenic fungi, and to methods of controlling diseases on useful plants.
- WO 2010/012793, WO 2017/207362, and WO 2019/105933 describe thiazole derivatives as pesticidal agents. Whilst many fungicidal compounds and compositions, belonging to various different chemical classes, have been/are being developed for use as fungicides in crops of useful plants, crop tolerance and activity against particular phytopathogenic fungi do not always satisfy the needs of agricultural practice in many respects.
- compositions comprising mixtures of different fungicidal compounds possessing different modes of action can address some of these needs (e.g., by combining fungicides with differing spectrums of activity).
- component (A) is a compound of formula (I): wherein X is N; Y is C-F or C-H; R 1 is hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 hydroxyalkyl, C 1 -C 3 alkoxyC 1 - C4alkyl, C 3 -C 4 cycloalkyl, C 1 -C 2 alkoxyC 1 -C 2 alkoxy, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkyl, C 1 - C 2 alkoxycarbonyloxy
- the weight ratio of component (A) to component (B) may preferably be from 100:1 to 1:100, from 50:1 to 1:50, from 20:1 to 1:40, from 15:1 to 1:30, from 12:1 to 1:25, from 10:1 to 1:20, from 5:1 and 1:15, from 3:1 to 1:10 or from 2:1 to 1:5.
- a method of controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, on useful plants or on propagation material thereof which comprises applying to the useful plants, the locus thereof or propagation material thereof a fungicidal composition according to the invention.
- fungicidal mixture compositions according to the invention may also include, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability).
- advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability.
- the presence of one or more possible asymmetric carbon atoms in a compound of formula (I) means that the compounds may occur in optically isomeric forms, i.e., enantiomeric or diastereomeric forms. Also atropisomers may occur as a result of restricted rotation about a single bond.
- the present invention includes all those possible isomeric forms (e.g.
- the present invention includes all possible tautomeric forms for a compound of formula (I), and also a racemic compound, i.e., a mixture of at least two enantiomers in a ratio of substantially 50:50.
- the compounds of formula (I) according to the invention are in free form, in oxidized form as a N-oxide or in salt form, e.g. an agronomically usable salt form.
- N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book “Heterocyclic N-oxides” by A. Albini and S.
- Y is C-F or C-H. In one set of embodiments, Y is C-F. In another set of embodiments, Y is C-H.
- X is N.
- R 1 is hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 hydroxyalkyl, C 1 -C 3 alkoxy C 1 - C4alkyl, C 3 -C 4 cycloalkyl, C 1 -C 2 alkoxyC 1 -C 2 alkoxy, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkyl, C 1 - C 2 alkoxycarbonyloxyC 1 -C 2 alkyl, C 1 -C 2 alkycarbonyloxyC 1 -C 2 alkyl, C 3 -C 4 alkynyloxy, C 1 -C 3 alkylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxyC 1 -C 2 alkyl, thienyl, or furanyl.
- R 1 is hydrogen, methyl, ethyl, isopropyl, methoxy, ethoxy, fluoromethyl, chloromethyl, bromomethyl, 2,2,2-trifuoroethyl, 1-hydroxyethyl, methoxymethyl, 1-methoxyethyl, 1-ethoxymethyl, 1- methoxy-1-methylethyl, cyclopropyl, methoxyethoxy, ethoxycarbonyl, 2-methoxy-2-oxo-ethyl, 2- methoxy-oxo-ethyl, 2-methoxy-oxo-propyl, propargyloxy, 1-methoxycarbonyloxy-ethyl, 1- ethoxycarbonyloxy-ethyl, 1-methylcarbonyloxy-ethyl, methylcarbonyloxymethyl, methylsulfanyl, ethylsulfanyl, isopropylsulfanyl, diethylamino,
- R 1 is hydrogen, methyl, ethyl, isopropyl, methoxy, ethoxy, fluoromethyl, 2,2,2- trifuoroethyl, 1-hydroxyethyl, 1-ethoxymethyl, cyclopropyl, methoxyethoxy, 2-methoxy-2-oxo-ethyl, 2- methoxy-oxo-ethyl, 2-methoxy-oxo-propyl, propargyloxy, 1-methoxycarbonyloxy-ethyl, 1- ethoxycarbonyloxy-ethyl, 1-methylcarbonyloxy-ethyl, methylcarbonyloxymethyl, isopropylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxymethyl, 1-benzyloxyethyl, 2-furanyl, or 2-thiophenyl.
- R 2 is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or HC(O)NH-.
- R 1 is C 1 -C 3 alkyl or C 1 - C3alkoxy. More preferably, R 1 is methyl or methoxy.
- R 3 is C3-C6cycloalkyl, wherein the cycloalkyl groups are optionally substituted with 1 or 2 groups represented by R 4 , or R 3 is a 6- to 10-membered non-aromatic spirocyclic carbobi-cyclyl ring system.
- R 3 is C 3 -C 4 cycloalkyl, wherein the cycloalkyl groups are optionally substituted with 1 or 2 groups represented by R 4 , or R 3 is a 6- to 8-membered non-aromatic spirocyclic carbobi-cyclyl ring system. More preferably, R 3 is cyclobutyl, 2,2-dimethylcyclobutyl or spiro[3.4]octanyl, and most preferably, cyclobutyl, 2,2-dimethylcyclobutyl, or spiro[3.4]octan-3-yl. R 4 is C 1 -C 3 alkyl.
- R 4 is methyl, ethyl or isopropyl. More preferably, R 4 is methyl.
- component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); [2-[[4-(cyclobutylcarbamoyl)-5-methyl-thiazol-2-yl]-(2,6-difluoro-4-pyridyl)amino]-1-methyl-2-oxo- ethyl] ethyl carbonate (compound X.02); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan
- component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] ethyl carbonate (compound X.04); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxypropanoyl)amino]-5-methyl-thiazole-4- carboxamide (compound X.07
- component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] ethyl carbonate (compound X.04); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- car
- component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- carboxamide (compound X.11); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-thiazole-4- carboxamide (compound X.12); 2-[acetyl-(2,6-difluoro-4-pyridyl
- component (B) is a compound selected from the group consisting of: azoxystrobin, trifloxystrobin, pyraclostrobin, picoxystrobin, coumoxystrobin, metyltetraprole, cyproconazole, tebuconazole, difenoconazole, hexaconazole, propiconazole, fenhexamid, prothioconazole, mefentrifluconazole, prochloraz, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, bixafen, penthiopyrad, inpyrfluxam, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, aci
- component (B) is selected from the group consisting of: azoxystrobin, trifloxystrobin, pyraclostrobin, picoxystrobin, coumoxystrobin, metyltetraprole, cyproconazole, tebuconazole, difenoconazole, hexaconazole, propiconazole, fenhexamid, prothioconazole, mefentrifluconazole, prochloraz, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, bixafen, penthiopyrad, inpyrfluxam, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, acibenzolar-
- component (B) is a compound selected from the group consisting of: azoxystrobin, trifloxystrobin, metyltetraprole, difenoconazole, hexaconazole, propiconazole, prothioconazole, mefentrifluconazole, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, acibenzolar-S-methyl, chlorothalonil, mancozeb, mandipropamid, oxathiapiprolin, fluazinam, fludioxonil, cyprodinil, metalaxyl-M, aminopyrifen, fol
- Example B10 Sclerotinia sclerotiorum / liquid culture (cottony rot) Mycelia fragments of a newly grown liquid culture of the fungus are directly mixed into nutrient broth (Vogel’s minimal media) containing 200 ⁇ Mol SHAM. After placing a (DMSO) solution of test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal material is added. The test plates are incubated at 24 °C and the inhibition of growth is determined photometrically 3-4 days after application. The following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test when compared to the untreated control under the same conditions, which showed extensive disease development.
- DMSO DMSO
- Example B11 Blumeria graminis f. sp. tritici (Erysiphe graminis f. sp. tritici) / wheat / leaf disc preventative (Powdery mildew on wheat)
- Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compounds diluted in water. The leaf disks are inoculated by shaking powdery mildew infected plants above the test plates 1 day after application.
- the inoculated leaf disks are incubated at 20 °C and 60% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness in a climate chamber and the activity of the compounds is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6 - 8 days after application).
- the following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test when compared to the untreated control under the same conditions, which showed extensive disease development.
- Example B12 Puccinia recondita f. sp. tritici / wheat / leaf disc preventative (Brown rust) Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compounds diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments are incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 - 9 days after application).
Abstract
Description
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Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2021284956A AU2021284956A1 (en) | 2020-06-03 | 2021-05-27 | Fungicidal compositions |
EP21728570.9A EP4161277A1 (en) | 2020-06-03 | 2021-05-27 | Fungicidal compositions |
US18/000,014 US20230270114A1 (en) | 2020-06-03 | 2021-05-27 | Fungicidal compositions |
CR20220616A CR20220616A (en) | 2020-06-03 | 2021-05-27 | FUNGICIDE COMPOSITIONS |
CN202180040155.6A CN115697063A (en) | 2020-06-03 | 2021-05-27 | Fungicidal compositions |
CA3178082A CA3178082A1 (en) | 2020-06-03 | 2021-05-27 | Fungicidal compositions |
MX2022015065A MX2022015065A (en) | 2020-06-03 | 2021-05-27 | Fungicidal compositions. |
KR1020227044991A KR20230019126A (en) | 2020-06-03 | 2021-05-27 | fungicidal composition |
JP2022574142A JP2023527894A (en) | 2020-06-03 | 2021-05-27 | Bactericidal composition |
BR112022024658A BR112022024658A2 (en) | 2020-06-03 | 2021-05-27 | FUNGICIDAL COMPOSITIONS |
IL298217A IL298217A (en) | 2020-06-03 | 2021-05-27 | Fungicidal compositions |
CONC2022/0016858A CO2022016858A2 (en) | 2020-06-03 | 2022-11-24 | fungicidal compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP20178040.0 | 2020-06-03 | ||
EP20178040 | 2020-06-03 |
Publications (2)
Publication Number | Publication Date |
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WO2021244951A1 true WO2021244951A1 (en) | 2021-12-09 |
WO2021244951A9 WO2021244951A9 (en) | 2022-01-13 |
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ID=70977432
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Application Number | Title | Priority Date | Filing Date |
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PCT/EP2021/064261 WO2021244951A1 (en) | 2020-06-03 | 2021-05-27 | Fungicidal compositions |
Country Status (17)
Country | Link |
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US (1) | US20230270114A1 (en) |
EP (1) | EP4161277A1 (en) |
JP (1) | JP2023527894A (en) |
KR (1) | KR20230019126A (en) |
CN (1) | CN115697063A (en) |
AR (1) | AR122482A1 (en) |
AU (1) | AU2021284956A1 (en) |
BR (1) | BR112022024658A2 (en) |
CA (1) | CA3178082A1 (en) |
CL (1) | CL2022003410A1 (en) |
CO (1) | CO2022016858A2 (en) |
CR (1) | CR20220616A (en) |
IL (1) | IL298217A (en) |
MX (1) | MX2022015065A (en) |
TW (1) | TW202200014A (en) |
UY (1) | UY39241A (en) |
WO (1) | WO2021244951A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023099460A1 (en) * | 2021-12-02 | 2023-06-08 | Syngenta Crop Protection Ag | Fungicidal compositions |
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2021
- 2021-05-27 US US18/000,014 patent/US20230270114A1/en active Pending
- 2021-05-27 JP JP2022574142A patent/JP2023527894A/en active Pending
- 2021-05-27 MX MX2022015065A patent/MX2022015065A/en unknown
- 2021-05-27 AU AU2021284956A patent/AU2021284956A1/en active Pending
- 2021-05-27 WO PCT/EP2021/064261 patent/WO2021244951A1/en active Application Filing
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Cited By (1)
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